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Bridgeway Bible Dictionary
Although brought up a slave in Egypt, Caleb proved himself a responsible leader once the people of Israel began to organize themselves on the journey to Canaan. Within a short time he became one of the leaders of his tribe, Judah.
On the journey to Canaan
When Moses chose twelve representatives (one from each tribe) to go to Canaan and spy out the land, Caleb was the person chosen from the tribe of Judah (Numbers 13:2; Numbers 13:6; Numbers 13:17-20). At that time he was forty years of age (Joshua 14:7).
The spies returned with a report that although Canaan was a fertile land, its inhabitants were fearsome, particularly the giant people of Anak who lived in the region of Hebron (Numbers 13:21-29; see ). This report immediately discouraged the people from going ahead with the attack, but Caleb spoke up boldly, believing that in God’s strength they could overcome the enemy (Numbers 13:30). The people, however, chose to accept the opinion of the unbelieving spies. They refused to trust God, and rebelled against the leadership of Moses (Numbers 13:31-33; Numbers 14:1-4). Only Joshua, the spy who went as the representative of the tribe of Ephraim, supported Caleb (Numbers 14:6-9).
God responded to the people’s rebellion by announcing that, since they did not want to enter Canaan, they would have their wish. During the next forty years all who were at that time twenty years of age or over (except Caleb and Joshua) would die in the wilderness (Numbers 14:28-35).
When, forty years later, a new generation had grown up and the people were about to enter Canaan, Moses appointed one leader from each of the twelve tribes to assist the new leader Joshua and the high priest Eleazar in the division of the land. Caleb was again chosen to represent Judah (Numbers 34:16-19).
Life in Canaan
After several years of battle, Canaan belonged to Israel and was divided between the twelve tribes. Groups of unconquered Canaanites were still scattered throughout the country, but each Israelite tribe was responsible for overcoming the enemies within its territory (Joshua 13:1-7; cf. Joshua 15:63; Joshua 16:10; Joshua 17:12; Joshua 17:18).
Caleb was now eighty-five years of age, but he was ready to show that his faith and courage were as strong as they had been forty-five years earlier. The people of Anak, whom the Israelites had once been afraid to fight, still occupied Hebron, the region that had been allotted to Caleb within the tribal territory of Judah. Caleb conquered them and took possession of their towns (Joshua 14:6-15; Joshua 15:13-14).
The boldness of Caleb helped to develop the faith and courage of others. Having set an example by his conquest of Hebron, he offered his daughter as a wife to any man who could conquer the neighbouring town of Debir. The conqueror was Othniel, who later became a great leader in Israel (Joshua 15:15-19; Judges 3:9-11).
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Fleming, Don. Entry for 'Caleb'. Bridgeway Bible Dictionary. https://www.studylight.org/dictionaries/eng/bbd/c/caleb.html. 2004.